Since there is nothing now, you will have to run all utilities to the site and construct everything (foundation, roof, walls, and all interior finishes) I would definitely call some GC's and get a better ballpark figure and be positive the city will allow you to construct.

Insurance will cover mostly new flooring & painting on the walls, but that's about it.  

I've even had issues with lender requiring repair for holes in interior wall from a removed speaker system, holes in carpet exposing slab, oven not working at appraisal, so a lot of what many see as minor issues can cause lender to not approve the loan.

The living room and dining room are connected by a partial wall with a large opening.

Some walls are stucco so need patching where has came off, flooring put down in addition (still plywood on floor), etc.Thanks for reading my long story!

The Podcasts are incredible and it's apart of my running routine.

Finally, I am considering adding wi-fi and front desk and somehow section off or partition spaces, either with drywall or pre fab removable walls for offices.   

We have had the interior of those areas completely gutted (floors, walls, ceilings) and are waiting to start repairs.

There needs to be a full understanding of how the brick works within the "wall system".

There is no way to cut a window as the next building wall is touching the siding of my property.